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Synthesis and in vitro activity of novel 2-(benzylthio)-4-chloro-5-(1,3,4-oxadiazol-2-yl)benzenesulfonamide derivatives.

Brożewicz K, Sławiński J - Monatsh. Chem. (2012)

Bottom Line: Two series of novel 4-chloro-2-(benzylthio)-5-(1,3,4-oxadiazol-2-yl)benzenesulfonamides and their N-aroyl derivatives have been synthesized and evaluated for in vitro anticancer activity against the full NCI-60 cell line panel.Most of the compounds exhibited antiproliferative activity.Among them a compound bearing an N-(thien-2-ylcarbonyl) moiety showed broad-spectrum activity with 50% growth inhibition (GI50) values in the range of 2.02-7.82 μM over 50 cell lines. .

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Affiliation: Department of Organic Chemistry, Medical University of Gdańsk, Al. Gen. J. Hallera 107, 80-416 Gdańsk, Poland.

ABSTRACT

Abstract: Two series of novel 4-chloro-2-(benzylthio)-5-(1,3,4-oxadiazol-2-yl)benzenesulfonamides and their N-aroyl derivatives have been synthesized and evaluated for in vitro anticancer activity against the full NCI-60 cell line panel. Most of the compounds exhibited antiproliferative activity. Among them a compound bearing an N-(thien-2-ylcarbonyl) moiety showed broad-spectrum activity with 50% growth inhibition (GI50) values in the range of 2.02-7.82 μM over 50 cell lines.

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Mentions: The desired N-acylsulfonamides 4a–4j (Scheme 2) were prepared by carbodiimide-mediated coupling of aromatic carboxylic acids with sulfonamides [32–34] promoted by 4-(N,N-dimethylamino)pyridine (DMAP) in the appropriate solvent. In some cases crystalline 4-(N,N-dimethylamino)pyridinium N-heteroaroylsulfonamidates (3a–3c) were isolated and characterized, which by treatment with 10% (w/v) ethanolic p-toluenesulfonic acid (p-TSA) solution were converted to the desired N-acylsulfonamides 4a–4c.Scheme 2


Synthesis and in vitro activity of novel 2-(benzylthio)-4-chloro-5-(1,3,4-oxadiazol-2-yl)benzenesulfonamide derivatives.

Brożewicz K, Sławiński J - Monatsh. Chem. (2012)

  
© Copyright Policy
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4494775&req=5

Sch2:   
Mentions: The desired N-acylsulfonamides 4a–4j (Scheme 2) were prepared by carbodiimide-mediated coupling of aromatic carboxylic acids with sulfonamides [32–34] promoted by 4-(N,N-dimethylamino)pyridine (DMAP) in the appropriate solvent. In some cases crystalline 4-(N,N-dimethylamino)pyridinium N-heteroaroylsulfonamidates (3a–3c) were isolated and characterized, which by treatment with 10% (w/v) ethanolic p-toluenesulfonic acid (p-TSA) solution were converted to the desired N-acylsulfonamides 4a–4c.Scheme 2

Bottom Line: Two series of novel 4-chloro-2-(benzylthio)-5-(1,3,4-oxadiazol-2-yl)benzenesulfonamides and their N-aroyl derivatives have been synthesized and evaluated for in vitro anticancer activity against the full NCI-60 cell line panel.Most of the compounds exhibited antiproliferative activity.Among them a compound bearing an N-(thien-2-ylcarbonyl) moiety showed broad-spectrum activity with 50% growth inhibition (GI50) values in the range of 2.02-7.82 μM over 50 cell lines. .

View Article: PubMed Central - PubMed

Affiliation: Department of Organic Chemistry, Medical University of Gdańsk, Al. Gen. J. Hallera 107, 80-416 Gdańsk, Poland.

ABSTRACT

Abstract: Two series of novel 4-chloro-2-(benzylthio)-5-(1,3,4-oxadiazol-2-yl)benzenesulfonamides and their N-aroyl derivatives have been synthesized and evaluated for in vitro anticancer activity against the full NCI-60 cell line panel. Most of the compounds exhibited antiproliferative activity. Among them a compound bearing an N-(thien-2-ylcarbonyl) moiety showed broad-spectrum activity with 50% growth inhibition (GI50) values in the range of 2.02-7.82 μM over 50 cell lines.

Graphical abstract: .

No MeSH data available.